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Cheap flights from Boston (BOS) to Chicago (CHI)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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Cheap flights from Boston to Chicago in September , October 2026

29 Sep - 10 Oct $ 294.00
BOS
Boston
JetBlue Airways
1 STOPS
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
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28 Sep - 20 Oct $ 317.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
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26 Sep - 19 Oct $ 417.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates

Last minute flights from Boston to Chicago

29 Sep - 01 Oct $ 332.00
BOS
Boston
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
BOS
Boston
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28 Sep - 30 Sep $ 416.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
26 Sep - 30 Sep $ 508.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
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One-way flights to Chicago from Boston

9:23 AM - 9:23 AM
United Airlines
0 Stops
2h 52m
BOS - CHI
$ 199
Kiwi
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7:00 AM - 7:00 AM
JetBlue Airways
0 Stops
2h 48m
BOS - CHI
$ 206
Kiwi
Pick dates
7:00 AM - 7:00 AM
JetBlue Airways
0 Stops
2h 48m
BOS - CHI
$ 206
Kiwi
Pick dates

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.